Fifth Time's A Charm
by of self
Summary: Oliver examines five different situations where he has 'awkward' moments with Lilly and then draws conclusions. Lilly/Oliver.


Sorry, I know I haven't posted a Loliver in like donkey's ages. I should have done it as soon as WIDLAY came out but I just saw the episode and squealed and then sat on my bum. Possibly I'm the worst Loliver shipper ever. Anyhow here is my Loliver attempt brought about by trying to de-disneyfy them. Clearly that part failed.

Disclaimer - I don't own HM or Sleepy Hollow or Johnny Depp or Christoper Walken.

* * *

Lately things have been awkward with Lilly. And frankly it's beginning to bother him. Because he's Oliver and she's Lilly and awkward should feel like home. Instead it feels all…weird.

He supposes it because he and Lilly are being thrown together more often since Miley has been away _only_ forever filming Indiana Joanie. But the thing is he and she have always been thrown together, and at that time awkwardness wasn't so much of a problem. Before when they were alone, he was still a kid with a propensity for trouble and she was just a little girl with pigtails and a propensity for getting him into trouble.

But now, now things have changed. He's a somewhat decent looking teenager with a motor mouth and she's a pretty looking teenage skater girl who has just discovered the ability to smack him senseless.

Things as such are built for awkwardness and indeed awkwardness does abound.

But what he's unable to decide if it's the nice kind of awkward or the bad kind of awkward. So he decided that maybe he needs to look at all these different 'awkward' moments in terms of an experiment and then draw adequate conclusions. So here goes.

_Exhibit A –_

He and Lilly are sharing a smoothie at Rico's. Not an uncommon occurrence given the perpetual state of penury they have been in lately. Since both of them want to drink it at the same time, they both share it at the same time. They are sitting close enough and sipping on it and only when he reaches the end does Oliver notices that he's a few inches away from Lilly's face. Now would be the time for him to get the heck away because he's all up in Lilly's face but no, he doesn't move an inch even. Instead he finds himself admiring Lilly's face and its coloring of gold and pink. Her skin is sun-kissed and smooth and her cheeks are pink. It's exactly the color of the tea-rose his Nana used to grow. And it does look _so_ pretty.

A moment or two later he finds himself looking into Lilly's blue-gray eyes and he's now trying to figure out if her irises are flecked with hazel or green. His gaze travels a little further down and comes to rest on her lips. Her lips are a little pink and chapped and he comes to realize that they are just perfect. Perfectly kissable.

He would have moved on to the throat and then a little lower( just thinking of that makes him feel…tingly) but something clicks in his head and he hurriedly moves away when he realizes that he's been conducting a much too intimate observation of Lilly's face. Thankfully Lilly doesn't notice but for the rest of the day he can't bring himself to look her straight in the eye and see all her lovely features come into play.

And by the way, her irises happen to be flecked with green.

_Conclusion – _

This would be a nice kind of awkward, at least from his perspective. But from Lilly's it might seem a tad stalker-ish kind.

_Exhibit B –_

They are watching a horror movie, Sleepy Hollow to be exact and he just cannot bring himself to see the movie without jumping in fright every time the Headless Horseman makes an appearance.

In his defense and believe him when he says it, it's an impassioned defense, Christopher Walken is beyond creepy as the Horseman. The setting of the movie doesn't help either. Everything's pale, colorless and almost dead and everybody looks like they have waxen skin, the kind favored by the undead.

So it's no surprise that when Johnny Depp on a carriage is being chased by the Horseman who keeps hacking at the coach, he screeches and buries his head in Lilly's lap because he's sure that Johnny Depp's Inspector Ichabod Crane's death is evident.

A few moments later he lifts his head up and finds Lilly looking at him quizzically. He colors and mumbles something about scary movies and being scared and spends the rest of the movie keeping strictly to the side of the invisible line between him and Lilly that he's drawn for himself. And though sometimes he wants to bury his head in Lilly's lap because it's so warm and comforting there, he doesn't because that is _so_ not done.

The only good thing from this whole fiasco is that Johnny Depp's Ichabod Crane is not a man who sets high standards of masculinity. The sight of blood makes him faint and at the end of the movie Mr. Depp does swoon in a very un-man like manner.

This cheers Oliver up immensely because that's makes it one less fictional hero to live up too.

_Conclusion –_

This is the bad kind of awkward. Scary movies call for the old arm-stretching trick, though he's sure Lilly can hold her own against any monster. But it would have been nice to pull it off without a hitch. However him diving into her lap like a frightened bunny, what's up with that? Whatever happened to his manly man-ness?

Went down the toilet that's what.

_Exhibit C –_

He's walking with Lilly in the hallways when he see's Pucas strolling down the hallway and blowing kisses at every girl in sight. He then has the gall to look at Lilly and blows one at her. Lilly's face crumples and her pretty blue-grey eyes well up with tears. Oliver doesn't know what comes over him. Maybe he finally grew a pair as his Granddad would say and he walks up to Lucas and punches him hard in the face. Moments later Lucas is sporting a brilliantly purple shiner and he's being dragged off by Ms. Krunkle to the detention room. But all this is worth it when he sees' Lilly looking at him like he's some kind of hero.

Okay, that wasn't the awkward moment but that was just the build up to it. In the evening, when he reaches home, there's Lilly waiting for him on the doorstep. Both of them stare at each other for a while and Lilly slowly ventures forward and kiss him a kiss on the cheek. He doesn't know what to say and she seems tongue tied and both of them look at each other for a few more moments before taking off in different directions.

_Conclusion –_

That was the nicest kind of awkward that has ever happened to him. And that kiss, that was pure heaven. Even better than the chocolate truffle cake his mother makes.

_Exhibit D -_

In hindsight, he should have knocked on the door instead of just walking in. But since when has he ever knocked at Lilly's door because of the whole mi casa et su casa principle that he and Lilly employ, so he just breezes in, sandwich transferring steadily from hand to mouth only to have his heart and his brain arrested by the sight in front of him.

The sandwich falls out of his mouth half masticated and he's pretty sure he's drooling because this seems like every wet-dream and fantasy rolled into one. Lilly standing there in lacy lingerie with her hair open and tousled and her skin a lovely shade of light golden brown. The expression is on her face is one of shock.

For a moment there's a stunned silence in the room and Oliver cannot even hear himself breathe because if humanly possibly, he's just stopped breathing.

Suddenly the air is rent with shrieks. Lilly shrieks, he shrieks and this goes on for quite a while before he hurriedly comes to his senses and stumbles out of the room. He makes his way down the stairs and out of the backdoor and spends the rest of the afternoon lying on the beach and trying to get rid of the image of a scantily clad Lilly from his mind. No such luck though because it's become a permanent fixture.

Also he may have just lost his best friend of all time over a simple issue of 'please knock before you enter a bedroom'.

Eff you life.

_Conclusion –_

Bad awkward doesn't even begin to cover it. Disastrous would be a much more accurate summation of the whole situation.

_Exhibit E –_

This isn't an awkward moment per say. It's the aftermath of exhibit D. It should be classified as a torturous moment. Okay it _should_ be classified as _awkward_ torturous moment. Because here he is waiting for Lilly at Rico's and drinking a strawberry smoothie all by his lonesome self. It sucks firstly because there's no pretty face to gaze at and secondly because he knows that the smoothie is going to come out as soon as he finishes it. Worrying about what Lilly's reaction to him will be has made his upchuck reflex very sensitive.

He waits for over an hour before Lilly turns up. And then to welcome her, he empties the contents of his stomach before her feet. It would be safe to say he didn't mean for things to go this way. It's just the beginning and already things are hopelessly deviating from the plan which was to clutch at her feet and grovel and apologize and beg for forgiveness.

This wouldn't be categorized as awkward but it would be definitely categorized as a torturous agonizing slowly moving moment. It's a mark of their friendship that Lilly doesn't run away screeching but instead helps him up, gives him water to drink and some wet-wipes.

He sits down at the table and faces her looking a little pale and sweaty and waits for the onslaught of insults about his lack of manners and perverted nature in general. He waits but nothing comes and he thinks that maybe he has to make the first move.

"Lilly about that incident, I'm-" and that's where Lilly cuts him off.

"Don't say you are sorry," she pleads, biting on her lip so hard that he can see the tiniest drop of blood appear on her lip. He's equal parts stunned and elated. But he has to say something that lets her know what he exactly feels. She has a right to know.

"I am sorry for invading your privacy Lilly," he catches her hand to prevent her from bolting and he isn't being cruel here because he _needs_ to her to hear him out, "but I will never ever regret walking in on you."

She looks as stunned as he did. Slowly an infectious smile breaks out across her face and he finds himself grinning too. All those feelings of nervousness and apprehension magically disappear and he's feeling as light as a soufflé.

Both of them are slowly leaning in and it's like one of those clichéd movies where everything is perfect. Except instead of lips meeting, noses bump and the aim is a little off as his lips land on the side of her lips.

Awkward.

That only makes her giggle and him blush and they try the second time because it's a charm and all that nonsense or something to that effect. This time it's perfect and it's been everything he's been dreaming of.

_Conclusion –_

If you look objectively at the whole scenario, you could classify it as awkward he supposes but to him this is perfect despite everything that happened. However he ultimately has to bow down to the dictates of science and classify this as something. So after weighing all the pro's and cons of it all he discovers that this would most definitely be classified as awkward.

However it was best kind of awkward ever, so he's good.

_-fin-_

_

* * *

_

This is how I'm supposed to write my psychology experiments. And it usually ends up being a pain but here it was fun.

Anyhow do review with your thoughts, and feel free to tell me I'm a nut-job who can't write. You will be right on both accounts. :)


End file.
